(2R,3R)-3-Benzyloxy-1-tert-butyldimethylsilyloxy-2-methylsulfonyloxy-3-(2-thiazolyl)-1,2,3-propanetriol

Base Information

• Chemical Name: (2R,3R)-3-Benzyloxy-1-tert-butyldimethylsilyloxy-2-methylsulfonyloxy-3-(2-thiazolyl)-1,2,3-propanetriol
• CAS No.: 119991-27-4
• Molecular Formula: C₂₀H₃₁NO₅S₂Si
• Molecular Weight: 457.687
• Mol file: 119991-27-4.mol

Synonyms:(2R,3R)-3-Benzyloxy-1-tert-butyldimethylsilyloxy-2-methylsulfonyloxy-3-(2-thiazolyl)-1,2,3-propanetriol

Chemical Property of (2R,3R)-3-Benzyloxy-1-tert-butyldimethylsilyloxy-2-methylsulfonyloxy-3-(2-thiazolyl)-1,2,3-propanetriol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R)-3-Benzyloxy-1-tert-butyldimethylsilyloxy-2-methylsulfonyloxy-3-(2-thiazolyl)-1,2,3-propanetriol

There total 3 articles about (2R,3R)-3-Benzyloxy-1-tert-butyldimethylsilyloxy-2-methylsulfonyloxy-3-(2-thiazolyl)-1,2,3-propanetriol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

methanesulfonyl chloride (124-63-0) + (1R,2R)-1-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-thiazol-2-yl-propan-2-ol (119991-41-2) → (2R,3R)-3-Benzyloxy-1-tert-butyldimethylsilyloxy-2-methylsulfonyloxy-3-(2-thiazolyl)-1,2,3-propanetriol (119991-27-4)

Guidance literature:

With triethylamine; In dichloromethane; for 2h;

DOI:10.1055/s-1988-27671

Reference yield:

(1R)-1-O-benzyl-2,3-O-isopropylidene-1-(2-thiazolyl)-D-glycitol (103795-11-5) → (2R,3R)-3-Benzyloxy-1-tert-butyldimethylsilyloxy-2-methylsulfonyloxy-3-(2-thiazolyl)-1,2,3-propanetriol (119991-27-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / aq. CF₃CO₂H / 0.25 h / Ambient temperature

2: 84 percent / imidazole / CH₂Cl₂ / 4 h

3: 98 percent / Et₃N / CH₂Cl₂ / 2 h

With 1H-imidazole; triethylamine; trifluoroacetic acid; In dichloromethane;

DOI:10.1055/s-1988-27671

Reference yield:

(2R,3R)-3-Benzyloxy-3-(2-thiazolyl)-1,2,3-propanetriol (119991-26-3) → (2R,3R)-3-Benzyloxy-1-tert-butyldimethylsilyloxy-2-methylsulfonyloxy-3-(2-thiazolyl)-1,2,3-propanetriol (119991-27-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / imidazole / CH₂Cl₂ / 4 h

2: 98 percent / Et₃N / CH₂Cl₂ / 2 h

With 1H-imidazole; triethylamine; In dichloromethane;

DOI:10.1055/s-1988-27671

upstream raw materials:

methanesulfonyl chloride

(1R,2R)-1-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-thiazol-2-yl-propan-2-ol

(1R)-1-O-benzyl-2,3-O-isopropylidene-1-(2-thiazolyl)-D-glycitol

(2R,3R)-3-Benzyloxy-3-(2-thiazolyl)-1,2,3-propanetriol

Downstream raw materials:

Methanesulfonic acid (1R,2R)-2-benzyloxy-1-hydroxymethyl-2-thiazol-2-yl-ethyl ester

(1R,2S)-1-Benzyloxy-2,3-epoxy-1-(2-thiazolyl)propanol

(1R,2S)-1-Benzyloxy-1-(2-thiazolyl)-1,2-propanediol

(2S,3R)-1,3-Dibenzyloxy-3-(2-thiazolyl)-1,2,3-propanetriol